Applied Systems Executive and Leadership Team

May, 2026

Leadership Overview

Applied Systems has 5 executives leading key functions including strategy, finance, technology, marketing, and operations.

Driven by innovation, Applied Systems provides essential cloud-based software solutions for the insurance industry, empowering agencies and brokerages across North America and Europe with robust management systems.

Leadership Roles at Applied Systems

  • Chief Executive Officer - Graham Blackwell
  • Chief Financial Officer - Brittany Smith
  • President & Founder - Henry Orejuela
  • Chief Technology Officer - Keith Olson
  • Chief Marketing Officer - Courtney Rains
  • Graham Blackwell - Chief Executive Officer

    Graham Blackwell, the Chief Executive Officer at Applied Systems, directs the company's overall strategic vision and operational execution. Blackwell guides the enterprise in its mission to deliver advanced cloud-based software solutions specifically for the insurance sector. This leadership involves overseeing all business units to ensure alignment with market demands and technological advancements. Blackwell's focus remains on expanding the company's global reach within the United States, Canada, the Republic of Ireland, and the United Kingdom. By fostering a culture of innovation, the Chief Executive Officer drives the development of agency and brokerage management systems that enhance client efficiency and profitability. Graham Blackwell ensures Applied Systems maintains its position as a leading provider in the financial technology space.
    Graham Blackwell

    Brittany Smith - Chief Financial Officer

    Brittany Smith, the Chief Financial Officer at Applied Systems, manages all fiscal operations and financial strategy. Smith oversees budgeting, forecasting, and financial reporting, ensuring the company's fiscal health and sustainable growth. This role involves close collaboration with other executive leaders to allocate resources effectively across product development, market expansion, and operational improvements. The Chief Financial Officer plays a critical part in evaluating investment opportunities and managing financial risks inherent in the global software market. Brittany Smith's expertise supports the company's expansion into key regions like the United States, Canada, the Republic of Ireland, and the United Kingdom. By maintaining stringent financial controls, Smith ensures Applied Systems meets its revenue targets and profitability goals.
    Brittany Smith

    Henry Orejuela - President & Founder

    Henry Orejuela, the President & Founder at Applied Systems, provides foundational leadership and strategic direction, drawing on extensive industry experience. Orejuela's role involves guiding the company's long-term vision and fostering relationships with key stakeholders within the insurance technology landscape. As President, Orejuela ensures the company's core mission of delivering essential cloud-based software solutions remains paramount. This leadership extends to overseeing strategic partnerships and market development initiatives across North America and Europe. Henry Orejuela's deep understanding of the insurance industry informs the ongoing evolution of agency and brokerage management systems. The President & Founder's commitment drives Applied Systems' sustained success and market influence.

    Keith Olson - Chief Technology Officer

    Keith Olson, the Chief Technology Officer at Applied Systems, spearheads the company's technological innovation and infrastructure development. Olson directs the engineering and product development teams, focusing on enhancing the cloud-based software solutions for the insurance industry. This leadership involves architecting scalable and secure systems that meet the evolving needs of agencies and brokerages. The Chief Technology Officer is responsible for the company's technology roadmap, ensuring robust performance and seamless integration of new features. Keith Olson's strategic oversight guides the technical teams in delivering cutting-edge agency and brokerage management systems. By championing technological advancements, Olson ensures Applied Systems remains at the forefront of the insurtech sector.

    Courtney Rains - Chief Marketing Officer

    Courtney Rains, the Chief Marketing Officer at Applied Systems, drives the company's global marketing strategy and brand presence. Rains oversees all marketing initiatives, including product positioning, lead generation, and customer engagement across key markets in the United States, Canada, the Republic of Ireland, and the United Kingdom. This role involves developing comprehensive campaigns that highlight the value of Applied Systems' cloud-based software for insurance agencies and brokerages. The Chief Marketing Officer collaborates closely with sales and product teams to ensure marketing efforts directly support business objectives and revenue growth. Courtney Rains' leadership focuses on expanding market awareness and solidifying Applied Systems' reputation as an industry leader. By executing targeted marketing strategies, Rains enhances customer acquisition and retention.

    Explore Leadership Teams in Financial Software

    Frequently Asked Questions Regarding Applied Systems Top Executives and Leadership Team

    Who leads Applied Systems?
    Applied Systems is led by Graham Blackwell (Chief Executive Officer), along with executives such as Brittany Smith (Chief Financial Officer) and Henry Orejuela (President & Founder).
    Who is part of Applied Systems’s executive team?
    The executive team of Applied Systems includes leaders such as Graham Blackwell (Chief Executive Officer), Brittany Smith (Chief Financial Officer), Henry Orejuela (President & Founder) and other senior executives.
    How many executives does Applied Systems have?
    Applied Systems has 5 executives leading key business areas.
    What roles are included in Applied Systems’s leadership team?
    The leadership team of Applied Systems includes roles such as Chief Executive Officer, Chief Financial Officer, President & Founder, Chief Technology Officer, Chief Marketing Officer.